Methylamine → [5-Bromo-2-(3,4-dichloro-phenoxy)-benzyl]-methyl-amine

HRID 2188266ノート

反応式

HRID 2188266 の反応式
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[C:8]([CH:11]=1)[CH:9]=O>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)=[C:8]([CH:11]=1)[CH2:9][NH:2][CH3:1]

参加物

5

反応物 2

HCID 6329MethylamineHCID 120170305-Bromo-2-(3,4-dichlorophenoxy)benzaldehyde

生成物 1

HCID 9947009[5-Bromo-2-(3,4-dichloro-phenoxy)-benzyl]-methyl-amine

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 702Ethanol溶媒2 回

実験手順

Under N2, a solution of methylamine (2.9 mL, 5.8 mmol, 2.0 M solution in CH3OH) in 20 mL of ethanol was treated with titanium (IV) isopropoxide (1.7 mL, 5.8 mmol) at room temperature. After 5 min., a suspension of 5-bromo-2-(3,4-dichlorophenoxy)-benzaldehyde (1.0 g, 2.9 mmol, the title compound of Preparation 1) in 20 mL of ethanol was added and stirred for 16 hr at room temperature. Sodium borohydride (0.165 g, 4.4 mmol) was then added and stirring was continued for an additional 24 hr, at which time the reaction was quenched by the addition of 5 mL of 6 N HCl and 5 mL of water, stirred for 30 min and made basic by the addition of saturated aqueous Na2CO3. The resulting mixture was extracted with EtOAc, and the organic extracts were clarified by filtration throught diatomaceous earth (d.e.), washed with saturated NaCl, dried over Na2CO3and concentrated in vacuo to a clear oil, 0.987 mg.

出典と根拠

ORDレコード
ord-8b444bedc36d4c3bbe788d9c6cda7195
出典データセット
uspto-grants-2002_06
特許番号
US06410736B1

反応ノート

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